Pharmaceutical product.



UNITED STATES PATENT OFFICE.

WALTER SGHOELLER, OI AND WALTHER SCHBAU'I'H, F IBEBLIH- HALENSEE,GERMANY, ASSIGNOBB TO FABBENFABBIKEN VORM. FRIEDR. BAYER a co., ormmnnn, onmmr.

A ObRPOB-L'IION 01' GERMANY.

I'HABHLOZ EUTIGAL PRODUCT.

11o Drawing.

To all whom it may concem:

Be it known that we, WALTER Scnonrmgn and WAL'IHER Sonnau'rn, doctors ofPhllosophy, chemists, citizens of the German Empire, residing,respectively, at Charlottenburg, near Berlin, and.- Berlin-Halensee,Germany, have invented new and useful Improvements in New PharmaceuticalProducts, of which the following is a specification.

Our invention refers to the production of mercury substituted esters ofcarboxyhc tion of acids which contain in their molecule an unsaturatedcarbon chain, that is substances of the type acn-caacoon in which Ameans an organic radical attached to carbon and R an alkyl or arylradical. Such esters have proven to be val uable therapeutic agents.

For the filreparation of our new substances we ow salts of mercury toreact upon the above defined esters in alcoholic solvents. Besides purealcohol, either a mixture of alcohol and water or, other saturated withwater have proved to be suitable solvents. Among the salts of mercury tobe employed those are preferred whic are soluble in alcohol, namelymercuric acetate and mercuric chlorid. The mercury substituted glycerinesters of the higher unsaturated fatty acids are of especial value asthere utic agents. For the preparaese esters it is not nry that theglycerin esters should be employed in ure state, theymay be used in theform of ate. The fats are best dissolved in aqueouslmeth orethyl-alcohol or in a mixture of e y'l-alcohol and ether and allowed tostand with a quantity of an alcoholic solution of mercu salt, indicatedby Hiibls iodin number o the. fat employed, until tested with soda lye,mercuric oxid is not any more precipitated. In the same manner mercunclecithins can be produced provided that at least one of the fatty acidcomponents of the lecithin consists of an unsaturated fatty acid, forinstance oleic acid.

The new compounds are whitish odorless substances, which are soluble inalmhol. Their alkaline salts are soluble in wa- "Specification ofLetters Patent. imam Med December 10, mo. Serial no. seam.

Patented Dec. 26, 1911.

ter. They have proved to be valuable antisyphilitics of a mild actionand as they are not irritating nor corrosive, they are valuable forexternal and internal application and especially for subcutaneousinjection. They contain the mercu so firmly combined that on adding adiluted solution of caustic alkali or a cold solution of ammonium sulfidno precipitate is obtained. A solution of from 0.1-0.2 grams may be usedfor one subcutaneous injection.

In carry proceed as Hows, the parts being by weight Example 1: 5dparts'of the methylic ester of'cinnamic aci in 80% methylic alcohol areadded to "9.8 arts of mercury acetate dissolved in methy '0 alcohol. Themixture is allowed to stand, until a sample tested with soda lye doesnot give any recipitate of mercuric oxid. This is usua y the case afterabout 24 hours. The substituted mercury ester which probably is formedaccording to the following formula:

cmucn-cmcoocHH-Hrwmoomwutoncrystallizes out in compact crystals from thethus obtained solution and the rest is easily obtained by evaporizationof the mother liquor. The ester is soluble in water and in the ordinaryorganic solvents, it can be best crystallized from acetic ether. Fromthe a ueous solution of the ester the corresponding chlorid of theformula is slrecipitated in a crystalline shape on the ad 'tion ofhalogen salts.- In an analogous manner mercury compounds of almost allother known unsaturated esters mag be obtained in a purestate and aswell de ned chemical substances.

Exam le 2: 5 parts of the ethylester of oleic acid dissolved in amixture of ethyl alcohol, ether and water, are treated as abovewith 5parts of mercury acetate. The solution, after standing for three hoursis allowed to eva orate and the remaining 011 which is sligh y ellowishvery refractive and easily movab e, is washed with water.

out our invention we can The amount of mercury contained in the oil isabout 33 per cent. The product probably corresponds to the form aExample 3: parts of triolein are dissolved in a mixture of methyl andethyl alcohol or ether and water and treated with 25 parts of mercuryacetate as. above. After evaporation a yellowish, semi-fluid oil isobtained which 1s soluble in fatty vehicles. Instead of the ure trioleinmixed fats and oils, such as l inseed-oil, rapeseed-- oil, palm-oil,wool-fat, olein, margarin, olive-oil, whale-oil, etc., can be used. Butthese oils and fats must be preferably free from free fatty acids. Thequantities reuired for the reaction are easily calculated irom the iodinnumber.

Example 4: 5 parts of lecithin containing oleic acid in its molecule aretreated with 2 parts of mercury acetate as above. After about 24 hours amercury lecithin can be isolated from the solution as a dark coloredunctuous mass, insoluble in water but soluble in alcohol, benzene andacetone.

.We claim The herein described mercury substituted esters of carboxylicacids which contain in their molecule an unsaturated carbon chain whichare odorless compounds, soluble in alcohol, containing the mercury sofirmly combined that the aqueous solutions do not ive any precigitate onthe addition of diute caustlc so a lye or a cold solution of ammoniumsulfid; and bein apeutical agents, substantial y as described.

In testimony whereof we have hereunto set our hands in the presence oftwo subscribing witnesses.

WALTER SCHOELLER. WALTHER SCHRAUTH.

valuable ther-

